Preparation of glucosamine hydrochloride

Preparation of glucosamine hydrochloride

Alternative Names: D(+)Glucosamine, Hydrochloride; D(+)Galactosamine, Hydrochloride; D-Mannosamine hydrochloride; D-(+)-Glucosamine hydrochloride; D-(+)-Galactosamine hydrochloride;

The carapaces and claws of lobsters, which have been cleaned as far as possible mechanically, are digested for 24 hours with cold dilute hydrochloric acid. They may then be cut up easily and freed from adherent fibres and flesh. 100 g of the material thus prepared are covered in a porcelain dish with concentrated hydrochloric acid, and heated till gently boiling on a sand-bath. The chitin quickly goes into solution, and the liquid becomes dark in color. The liquid is evaporated until a considerable crystallization of glucosamine hydrochloride has taken place, then allowed to cool, filtered and washed with a little cold hydrochloric acid. The mother-liquor on further evaporation yields a second crop of crystals. To purify the salt it is dissolved in warm water, and the solution is concentrated till crystallization begins.

Introduction to the preparation of organic compounds, E. Fisher, 154-155, 1909

IUPAC Name

3-amino-6-(hydroxymethyl)oxane-2,4,5-triol;hydrochloride

InChI

InChI=1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H

InChI Key

QKPLRMLTKYXDST-UHFFFAOYSA-N

Canonical SMILES

C(C1C(C(C(C(O1)O)N)O)O)O.Cl

Depositor-Supplied Synonyms

D(+)Glucosamine, Hydrochloride, D(+)Galactosamine, Hydrochloride, D-Mannosamine hydrochloride, D-(+)-Glucosamine hydrochloride, D-(+)-Galactosamine hydrochloride, D-Glucosamine-1-13C hydrochloride, AC1MD4O7, Ambcb5152335, 2-Amino-2-deoxy-D -mannose, D-Galactosamine, Hydrochloride, SCHEMBL15541837, 3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Hydrochloride, MolPort-001-768-894, CCG-2258, .beta.-D-Galaltosamine hydrochloride, AG1030, NSC283301, AKOS009031374, AN-5853, MCULE-8889939994, NSC-283301, .beta.-D-Galactopyranose, hydrochloride, CA007706, Galactopyranose, hydrochloride, .beta.-D-, I04-0062, 3-amino-6-(hydroxymethyl)tetrahydropyran-2,4,5-triol hydrochloride, 14257-79-5

Removed Synonyms

chitosamine, D-Mannosamine, 2-Amino-2-deoxy-D-glucose, Chondrosamine hydrochloride, D-Glucosamine hydrochloride, D-Galactosamine hydrochloride, CID2830832, 2-Amino-2-deoxy-D-galactose hydrochloride, D-Glucose, 2-amino-2-deoxy-, hydrochloride, D-Galactose, 2-amino-2-deoxy-, hydrochloride, D-Glucose, 2-amino-2-deoxy-, hydrochloride (1:1), D-Galactose, 2-amino-2-deoxy-, hydrochloride (1:1), 1772-03-8, 5505-63-5, 66-84-2

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